As summer winds down in Chicago, restaurants and bars are pulling out all the stops with rooftop parties, boy band brunches, adult trivia nights, and Midwestern wine dinners.

Photo courtesy of Wow Bao

National Bao Day is a Thing!
It seems there’s a food holiday for everything nowadays, but one that stands out is National Bao Day. As a dumpling-lover, I’m here for it. And Wow Bao is celebrating accordingly by offering free lunch on August 22 in honor of the doughy holiday. Available at all locations, free lunches will be doled out (up to $10 value, let’s not go nuts) from 11 a.m. until 1 p.m.Details: August 22, 11 a.m.-1 p.m.

10th Anniversary Weekend Specials at Nana
One of the best—and most underrated—neighborhood restaurants in Chicago is celebrating a milestone as Nana enters its 10th year (!) in Bridgeport. The homey, family-run restaurant rooted in locally sourced Latin-inspired dishes is toasting the occasion with a handful of specials pulled from past menus, all of which helped solidify the restaurant as a beloved staple. These include chicken tinga empanadas, Nana’s fried chicken sandwich, and the Sonora skillet with chorizo, vegetables, hash browns, eggs, and salsa verde. There will also be peach whiskey sours and matcha horchata to drink.Details: Specials available during regular business hours August 23-25

Tanta Turns Six
In other anniversary news, Tanta is turning six in River North, and to celebrate, the perpetual hot spot is throwing a rooftop party with current chef Giancarlo Valera and former chef Jesus Delgado. Look for a made-to-order cebiche station, a lechon carving station, live music, and specialty cocktails featuring Santiago Queirolo Pisco, Fid Street Gin, and Pau Maui Vodka.Details: August 26, 6-9 p.m.; $75

Photo by Anthony Tahlier/Courtesy of AceBounce

Boy Band Brunches at AceBounce
Calling all Backstreet Boys/N*Sync fans, AceBounce has a special brunch promo lined up that’s equal parts nostalgia and comfort food. The Boy Band Brunch series takes place every Saturday in August, featuring dishes like breakfast sausage casserole and loaded cronuts alongside boy band karaoke and trivia, a DJ, ping pong, and a Bloody Mary bar.Details: Saturdays in August, 12-3 p.m.; $49

9th Annual Shuck Off and Seafood Fest at Frontier
Let’s be honest: at this point, nine years in, Frontier’s annual Oyster Shuck Off and Seafood Fest is the bivalve equivalent of Lollapalooza. The yearly spectacle takes place August 26 this year, with local chefs vying for a $1,200 prize and the coveted title of “Chicago’s Fastest Oyster Shucker.” This year’s culinary talents come from the likes of GT Fish & Oyster, Cantina Laredo, Shaw’s Crab House, and others. For attendees, in addition to shucking entertainment, there will also be a crawfish and crab boil, an oyster happy hour, and a bevy of drink specials.Details: August 26, 5:30 p.m.; $35 (happy hour is open to the public with no cover, running 12-3 p.m.)

Rooftop BBQ Party at the Chicago Marriott Downtown Magnificent Mile
It’s sad to think that summer is winding down, but The Chicago Marriott Downtown Magnificent Mile’s rooftop barbecue party is a nice way to send out the season in style. Especially considering the hotel’s rooftop garden is typically not even accessible to the public. And the altruistic fact that the shindig is benefitting The Children’s Miracle Network. So you can drink beer, wine, and cocktails for a good cause, and feast on barbecue carrots, smoked shrimp, crispy short ribs, and cornbread with smoked cheddar and rooftop honey.Details: August 29, 5-8 p.m. on the 9th floor rooftop; $40

Photo courtesy of Kinton Ramen

Midwest Wine Dinner at Publican Quality Meats
Midwestern wines get their deserved time in the spotlight at this very special dinner, where six courses of food by chef de cuisine Rob Levitt are joined by regional wines from Michigan, Ohio, Wisconsin, and naturally, Illinois. With quality bottles coming from the likes of August Hill Winery, Mari Vineyards, and Wollersheim Winery, you might be surprised by how much you love it.Details: August 29, 7 p.m.; $127.04

Celebrate Labor Day at etta
What better way to punctuate another summer season than with a bottomless tub of rosé? Bucktown’s red-hot etta is throwing the Labor Day party of the year, with endless pink wine and hearty dishes like wood-fired pizzas, pastas, dry-aged rib-eyes, and the popular people-pleaser known as the “pig picnic.” The event is casual and first come, first serve, so hurry in.Details: September 2, 12 p.m.

Cool Off With Chilled Ramen
The dog days of summer are upon us, and while there’s plenty of great ice cream and cool treats around the city to indulge in, one dish that’s worth seeking out is tsukemen, aka chilled dipping ramen. It’s a bowl of chilled noodles tossed with ground white sesame seeds and sesame oil, served at Fulton Market newbie Kinton Ramen. The dish is adorned with pork belly and shredded nori, served with savory sauce for dipping.

Band of Bohemia’s 3rd Annual Caravan Art Festival
One of the most unique restaurant events of the season, Band of Bohemia’s annual Caravan Art Festival feels part carnival, part brewpub, as the parking lot next to the restaurant fills with artsy tents, jazz, hot dogs, and brats. Peruse the vendors outside before heading indoors for brunch or dinner.Details: September 8, 2 p.m.; $5 suggested donation

Photo courtesy of Band of Bohemia

Celebrate Grandparents Day With Sundae Funday
Speaking of holidays, you haven’t forgotten Grandparents Day, have you? With the holiday coming up September 8, Chicagoland Culver’s locations is offering an adorable promo that allows kids to celebrate with their grandparents in a truly sweet way: beginning September 8, 25 area outposts are offering a free frozen custard sundae to a lucky—and hungry—grandparent. The offer is limited to one per customer, dine-in only, and with the purchase of another frozen sundae. Because grandma or grandpa shouldn’t be dining alone on Grandparents Day, anyway. To make things even cuter, all participating Culver’s will have a life-size pop-up picture frame for selfie opportunities, with the hashtag #generationsunited to shoutout the company’s efforts to engage all generations. The free custard offer is available on the remaining Sundays in September.Details: Check out participating locations here

Adult Trivia Night at JoJo’s Milk Bar
I love a good racy trivia night, especially when it’s held in a fun, colorful space outfitted with a life-size Lite Brite Wall, board games, and Pac-Man machines. JoJo’s Milk Bar now hosts adult trivia nights on Wednesdays in its upstairs “Playroom.” As the suggestive name hints, the trivia is for mature audiences only.Details: Wednesdays, 7-10 p.m.